


Angel Escorts

by AlixxBlack



Series: Trope Challenge [19]
Category: Supernatural
Genre: Destiel - Freeform, F/M, Fake Dating, Fake Relationship, Flirty, M/M, Normal AU, escort AU, meet cute
Language: English
Status: Completed
Published: 2020-01-13
Updated: 2020-01-13
Packaged: 2021-02-27 07:34:06
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,571
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22233364
Author URL: https://archiveofourown.org/users/AlixxBlack/pseuds/AlixxBlack
Summary: Trope #8 of 30, per the list seen on Twitter in a series of tweets by @ selpukuPrompt:  ‘It’s a christmas party/thanksgiving/reunion/wedding and I said I’m bringing my bf/gf/fiancé when in fact I’m single, time to use an escort service pretending to be my significant other for the occasion’
Relationships: Castiel/Dean Winchester, Jessica Moore/Sam Winchester
Series: Trope Challenge [19]
Series URL: https://archiveofourown.org/series/1534436
Comments: 1
Kudos: 30





	Angel Escorts

**Author's Note:**

> Disclaimer: All credit where credit is due to the original author and publishing company. I am not writing this for any sort of profit in any way. The credit for the prompts to the original poster as well.
> 
> Disclaimer(b): The tag "normal au" indicates that this is a world without monsters, demons, etc, and shows Sam and Dean in a regular setting where they have "normal" lives like they reference in the show. Sam and Jess have an established relationship.

“What kind of service only posts the names of their escorts?” Dean growls at a man donning a tan trench coat sitting next to him on a bench.

The man in the trench coat keeps a blank face, but replies quickly. “I believe you made an assumption because the name of the company is Angel Escorts, so you made an assumption that females are often referred to as angels that Angel Escorts only contracted females.”

“I did not  _ assume _ that there were only females,” Dean spits back at him. “I used to call my brother an angel because he always did his homework and followed every rule.”

Trench coat smiles. “I understand. You do not want people to know that you are sexist.”

“I’m not sexist!” Dean shouts, yanking his hands up to his forehead and running both hands through his hair.

“But you are upset because I am not a female escort?” he asks, attempting to both clarify the issue and point out the lie Dean is telling himself.

Dean thinks really hard on the night he hired Cass, out of desperation. Sam and Jess were throwing a New Year’s Bash part at their place to celebrate Sammy making partner at his swanky law firm and Jess taking on a new role at the university as Department Head. They’d done so well for themselves all year that Dean sort of lied and said he had met someone that he thought could be “the one” and was super vague about the things that they did together and how they met.

It was a lie and that’s how he ended up hiring an escort. Apparently this weird man named Cass was the escort he thought was going to be a bombshell model type. Dean couldn’t even defend himself. None of the escorts on the website had genders listed, and half of them didn’t even use pictures in their profile. It was was a crapshoot.

“How many men work for your company then?” Dean barks his question in frustration. “Are you the only one?”

“Most of the other employees are androgynous, so our sex is only disclosed if the escort will be hired for intimate services, but that is all under the table. Your bid stated you needed a significant other for a party, so it was never brought to your attention because that is not the protocol,” Cass explains robotically, likely from having to explain this a number of times. Dean wonders how many people have hired Cass expecting him to be a woman.

Dean shakes his head, “Are you kidding me?”

“This is not a joke, Mister Winchester. Unfortunately, there are no refunds once an escort meets with the client, so I’m afraid you also cannot get your money back,” Cass, again, rattles off information like he’s been programmed to say it. His profile said he was comfortable in social situations but slight awkward when interacting with others, but Dean never would have guessed someone like Cass.

Dean looks at Cass who is watching him with wide eyes. It’s not that he doesn’t think that man is attractive, because he has a soft expression with a strong jaw and eyes as brilliant as the sky on a clear day. He has a decent enough build when the trench coat he’s wearing is hiding his body, and his style is crisp and simple. The women passing by can’t help by stare at him for just a little too long.

The issue is more that Dean hasn’t ever explored the possibility of a relationship with a man. He’s watched his fair share of adult films and enjoyed the male stars just as much as he’s enjoyed the female ones. Sexuality isn’t something that he’s ever labeled or thought of in a black-and-white frame of mind. Still, Dean has only ever dated women. He’s only ever slept with women… present.

Cass interrupts his thoughts, “You have been looking at me for a long time. It appears that you are trying to decide what to do about your party. I would be willing to hit you so that you can say you got in a fight and cannot make it.”

Laughing, Dean shoots him down. “Not happening.”

“You can take me and say that your girlfriend was cheating on you with me and we decided to dump her and attend the party together,” he suggests next.

“Not a bad idea, but,” Dean starts to say before he feels a hand squeezing his shoulder and he jumps to his feet, ready to take down whoever is touching him.

Of course, it’s just Sammy. “Fancy seeing you here. Too old to walk all the way to our condo?”

Dean hears Cass stand upright and reach around his body to shake Sammy’s hand. It only takes a second for Dean to start talking before Cass starts telling his porn-worthy excuse for why he was there instead of Dean’s supposed girlfriend. “This is my date tonight. Cass, this is my brother, Sam.”

“Date?” Sammy says through a sideways grin, keeping his gaze locked on Cass. Without either of them speaking or even looking at each other, it is obvious that Sammy is pleasantly surprised. “I thought you said you were seeing someone else?”

Dean can’t deny that Sammy is always mindful about the words he uses and how he says them. There is a reason he’s such a successful lawyer. Sammy calls himself an “attorney” which the fancier way of calling himself a lawyer, but Dean lets it slide. He knows Sammy’s roots, and them roots say he’s a lawyer.

“Well,” Cass starts, but Dean butts in before he gets too far.

“It’s kind of a messy story, and I didn’t tell anyone about it,” Dean says quickly, turning and making a face at Cass hoping to indicate that he should stay quiet.

Sammy shrugs his shoulders, “That’s cool. Maybe you could tell me that story on our way back to my place? Jess sent me out for some peppers because I guess we’re doing stuffed peppers now.”

“The party guests are arriving in thirty-five minutes,” the blurt comes out in the strange monotone that is becoming a bit of a quirky trait of Cass’s. Dean waits for Sammy’s reply but he makes a weird face. There’s something he’s not saying. However, Cas asks a question without a filter before Dean can even put the pieces together. “Is she having weird cravings already?”

Sammy’s eyebrows jump straight up. “Wha-wait? How did you know that?”

“You are already dressed in nice slacks and you are sweating, which means that you came out very quickly and in a rush. If you don’t have a good reason for making stuffed peppers, and you didn’t forget that you wanted to make them, then one of you must be craving them. Since you are the one who came to get them, I can’t help but think that you did it so that she didn’t have to be inconvenienced. With the party being so soon, it seems very unlikely to me that it would be a bother for either one of you to go out for the peppers, so there must be another reason that she could not -”

It dawns on Dean what Cass is saying and he turns to his brother faster than the speed of light. Grabbing his shoulders and shaking him, he asks the now-obvious question. “IS JESS PREGNANT?” 

Sammy shakes his head but then nods his head, shaking it immediately after that before hanging his head low. Dean shoves Sammy back, turns to Cass and stares him down. “Are you a mind reader? Do you have super powers?”

“No, I just can read people the way other people read books,” he explains bluntly.

“No, shit,” Dean scoffs in reply.

Sammy interjects, pleading with us. “Jess doesn’t want anyone to know yet. We were going to make an announcement in February on Valentine’s Day because that’s when we’re going to learn the gender of the baby.”

Cass smiles gently. “You’re going to have a healthy baby girl.”

When Dean sees Sammy’s face fall in defeat, he knocks his elbow into Cass’s side and begins cackling. Sammy says he’ll see them at the condo when they’re ready and leaves before Dean can make any comments or Cass can make any new observations. When his brother is out of earshot, Dean squares up to Cass and grins.

"You're awesome and we're going to have one helluva date tonight, partner," the remark rings with a southern twang, intentionally, and a laugh buried in the under breath of his words.

Cass grins and nods his head in reply. “I am happy to provide my services, Mister Winchester.”

“Just call me ‘Dean,’” he declares.

“I can do that,” the confirmation comes smoothly. It makes sense, since this is his profession. Still, Dean sees it as an opening. Or rather, as an opportunity.

“While we’re walking, maybe you can explain to me what might happen if an escort actually starts dating one of their clients,” the declaration is dripping with Dean’s usual romantic confidence, but with an unfamiliar tone of interest that is pulsing in his veins. There is something about Cass that has him intrigued, and just a little bit hungry for something he didn’t even know he wanted.

“Well,” Cas begins with a smile and twinkle in his eye that Dean is sure he’ll never forget.


End file.
